


Dean Can't Keep it Up

by WaywardAF67



Category: Supernatural
Genre: Anal Sex, Bottom Castiel, Drunk Dean Winchester, First Time, M/M, Masturbation, Porn With Plot, Rimming, Sex Toys, Smut, Top Dean Winchester
Language: English
Status: Completed
Published: 2018-08-25
Updated: 2018-08-25
Packaged: 2019-07-02 03:26:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,352
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15787980
Author URL: https://archiveofourown.org/users/WaywardAF67/pseuds/WaywardAF67
Summary: After walking in on Cas pleasuring himself, Dean can't get the image out of his head. In an attempt to forget, he goes in search of a hookup. After striking out several times, he learns that what he really wants might be waiting at home.





	Dean Can't Keep it Up

**Author's Note:**

> So head's up this has a bit of M/F. There is a tiny explicit scene of Dean having a fantasy of what he would do with a woman to clear his mind of Cas. Dean does find someone to hookup with, but I don't go into detail about them. So if you are a person that doesn't like reading Dean with others know that it's kind of in this fic, but not really. Destiel is endgame and the smut happens. :) 
> 
> Also, as always thanks to TrenchcoatBaby and EllenofOz for the edits.

Cas sighed, rocking back against the dildo suctioned to his headboard. Stroking his dick in rhythm with each thrust back against the silicone. He knocked the headboard against the wall as he fantasized Dean calling out his name. “Yes!” he cried out as the toy slid over his prostate. Just a few more strokes and––

“What the fuck, man?” Dean barked, gripping the doorknob.

Cas’ head jerked up just as pleasure ripped through his body. It was too late to stop his orgasm and he stared at Dean standing in his doorway, cum splashing over his hand.

He had enough sense to be embarrassed, but there was no saving face in the situation, so Cas calmly asked, “Did you need something Dean?”

The hunter stared at him mouth agape, taking a long moment to respond. “Ah, no. I don’t know. I just––I’m gonna go. Dinner. I’m gonna cook dinner.” Dean didn’t make a move to leave.

Cas was on his hands and knees, eyes trained on Dean, plastic dick still lodged in his ass. “It’s only four o'clock,  are you turning into an early bird?” Cas joked. He was proud of himself. Dean often uses humor to diffuse awkward situations, and though he wasn't particularly uncomfortable, he saw that Dean was.

Dean stumbled backward, hooking his thumb over his shoulder. “I’m gonna––” He didn't finish his sentence before walking out of Cas’ room, slamming the door behind him.

Cas pulled forward slowly, dislodging the dildo, and crawled across the bed where he stashed cleaning wipes. He would properly wash the toy later, but for the moment, he just swiped it, and himself, down with a few wipes.

He took his time getting dressed, wondering what he should say to Dean over their early dinner. Cas didn’t need to eat, but he enjoyed having a meal with the brothers when the three of them were home together.

 _Home._ Cas thought, wondering when the bunker became home and heaven became _someplace I used to live._

It was hours before Cas saw Dean again. He went to the kitchen, expecting Dean to be working on dinner as he said, but he only found the cap to a whiskey bottle and a missing tumbler from the shelf. Cas had sought him out but didn’t find him until closer to late evening, the usual time Dean started dinner.

“Hello, Dean,” Cas said walking up behind the other man, startling him, so much he jumped.

“Jesus,” Dean squeaked, spinning and ready to attack. He glared at his raised spatula and turned back to the frying hamburgers.

“Nope, just Cas.” The angel smirked and preened slightly. Proud of his joke.

“Smart ass,” Dean mumbled.

Cas leaned back against the counter, taking a moment to watch Dean work around the stove. He traded his spatula for an actual weapon as he began to slice a tomato. His posture was stiff, and Cas imagined he was still feeling uncomfortable about their _incident_ earlier.

“Dean, I am sorry about earlier. I know it’s embarrassing, but as you have told me many times, you should knock before entering someone’s room.”

Dean’s head jerked to the side on reflex, just as the knife was coming down over the tomato, slicing his finger open. “Fuck.”

Cas reached for Dean to heal his wound, and Dean’s eyes went comically large, crossing as Cas’ two fingers got closer to the other man’s forehead. Dean ducked out of the way, and bumped into the counter.

“Don’t be stubborn, Dean. Let me heal you or you’ll need stitches.” Cas stepped close, as Dean backed away. He looked terrified as he scowled at Cas’ fingers, still poised, ready for healing.

It took a second to click, but when Cas understood the horror on Dean’s face, a laugh bubbled up from deep in his throat. “You don’t have to worry, Dean, I’ve thoroughly washed my hands. Not to mention, that’s not the hand I––”

Dean threw up his bloody hand. “Stop. I don’t want to hear it.”

Cas took advantage of Dean’s distraction, and pressed two fingers against his head, healing the cut and removing any sign of blood.

“Why did you even let me in if you were in the middle of...that?” Dean asked, sagging against the counter.

“I didn’t let you in Dean, you walked in on me.”

The hamburgers sizzled, and Dean jumped up, wielding his spatula once again. “Yes, you did. I knocked and called out your name. You responded ‘yes’. That’s the universal word for come in, man.”

Cas thought back, not remembering hearing a knock. Though, he did recall that his fantasy version of Dean saying his name did sound awfully real. The pieces lined up, and Cas realized that he did indeed shout ‘yes’ after he knocked his bed against the wall and imagined Dean calling out his name.

Dean’s face lost all color as he too must have drawn the same conclusion. “Oh, god, you weren’t talking to me.”

“No, I was not. I was having an intimate moment of self-pleasure. I’m sorry you witnessed what you did.” Cas took a step back, realizing he had been crowding the other man.

Dean lifted the side of his mouth shrugging. “No man, it’s fine.”

 

***

 

It was not fine. It had been three days, and Dean still couldn’t shake the image of Cas on his hands and knees, cum coating his hand as he locked eyes with his own. It wasn’t as if he hadn’t caught Sam a few dozen times, it was just part of life on the road. It was always a little uncomfortable after, but they usually moved on after a few tense hours. True enough, he thankfully had never witnessed his brother climaxing, but it wasn’t like Cas was the same as Sam. He was family, sure, but not the kind of family Sam was.

Not to mention it wasn’t like he hadn’t seen a ton of guys coming. He watched porn all the time, and of course, there was that one time with Crowley and the triplets. Dean shivered, trying to shake off the memory.

It never occurred to him that Cas had needs or urges. He never mentioned it, and never tried to hook up with anyone while they were out at bars. Even when Sam and Dean both went home with someone, Cas always went straight back to the hotel.

So why had Cas never mentioned wanting to get laid? Dean could have been his wingman. He laughed at the phrase. As if an angel needed a wingman. Cas could just pull out his impressive wings if he wanted to impress someone.

Dean lay in bed several days after the _incident_ , thinking about how to help Cas find a date. It wasn’t like it would be hard. He was a good-looking guy, downright sexy if you were into the ruggedly handsome type. But he thought about all of Cas’ social awkwardness and decided it might have been for the best he hasn’t tried to bed a stranger. Maybe another hunter. Someone who knows he’s an angel, that could work.

He mentally scanned the list of hunters he knew. Not many women chose this life, and even fewer of them were single and of age. He had two names on his list when it dawned on him that Cas, probably didn’t strictly date women. He was taking what looked like a fucking ten-inch dildo when _the incident_ happened. Maybe he could call around and see if there were any hunters other than Jesse and Cesar who were into dudes. Maybe they knew of someone good for Cas. He wanted to call and check on the ranch anyway, it would be a good time to bring it up.

Satisfied with his plan, Dean rolled over and was asleep within minutes.

 

_“Dean, oh fuck Dean, harder.” Cas moaned as Dean thrust his hips forward._

_“Cas, I’m gonna––ah––fuck.”_

Dean jerked awake, as the tremors wracked his body. His mind was still fuzzy when he reached down and felt his cum-soaked boxers.

“Ah, fuck,” he groaned, throwing himself back against his bed. He hadn’t had a wet dream since he was a fucking horny teenager. And at––he reached over groggily and turned the clock towards himself––three forty-five in the morning he wasn’t going to allow himself to wonder why Cas was the star of his first wet dream in over twenty-five years.

He shucked his boxers, silently praying that this wasn’t the night the bunker got invaded. Rolling to his side, he laughed at the image of him running into the hall, Sam and Cas under attack while he was full on Donald Ducking it.

When morning came, Dean woke up rock hard with the image of Cas pushing back on the surprisingly realistic looking dildo fading from memory. He groaned, trying to clear his thoughts. He didn’t want to spend his nights dreaming about his best friend fucking himself on molded silicone. The least he could do would be to find Cas a real… _okay, that’s enough of that._

Dean jumped from his bed, forgetting he chose to go pantless in the middle of the night. He looked down at himself. Black t-shirt, socks, and raging hard-on jutting out. He couldn’t help the hysterical laughter that bubbled up from his throat. This thing, that one moment with Cas, was turning him into a crazy person.

Wrapping his dead guy robe around himself, Dean made a mad dash for the showers. The last thing he wanted was to physically run into Cas, dick first.

Though the showers were locker room style, they had divided sections with double layers of thick curtains. Sometimes when they got home from a hunt they didn’t have the energy to wait until the other one finished. Sam used the first shower, and Dean used the last. The showers were tucked behind a wall away from the row of urinals and toilet stalls. If Dean was showering alone, he never bothered to close the curtains. It made him feel...adventurous.

He twisted the cool metal knobs, adjusting the temperature to just under scolding. As steam filled his corner of the shower, Dean hung up his robe and climbed in. Hot water pounded over his shoulders, running down his back and caressing his ass. The warmth washing over his chilled skin made his body break out in goosebumps, and his nipples drew up tight.

It did nothing to help relieve the throbbing in his groin. He turned, letting the water pelt his chest. The droplets were racing down his torso, coating his balls and cock in a flood of warmth.

Tipping his head forward, Dean massaged his scalp, doing his best to avoid his erection. It wasn’t abnormal for Dean to jerk off in the shower, but given the last thing he remembered of his dream was Cas’ cum-coated hand, he wasn’t going to let himself.

But the more his hands rubbed over his body, spreading the crisp spring scent of his body wash, the harder his cock throbbed. Every inch of him screaming with desire.

With a hesitant, soapy hand, Dean gripped himself and began to stroke slowly. He tried lying to himself, saying it was just good hygiene, and he was only being thorough. But he wasn’t even fooling himself as he picked up the pace. Pumping his cock now with purpose.

His left hand braced against the slick tile, fingertips turning white as he tried to hang on to the wet surface. He set a perfect rhythm, the one he used when he needed to get off quickly, but still had a few extra moments to enjoy it. A release born of enjoyment, rather than need.

His fingers stroked his swollen flesh, gripping tighter as the end drew nearer. His left hand slid further up the wall as he leaned forward, pressing his entire chest against the tile.

The muscles in his forearm twitched as he stroked faster and faster. His head started to spin, and images of Cas fucking himself against his headboard took over his mind. The way Cas’ raspy voice groaned “Yes” before Dean walked in. Cas’ dark blue eyes boring into him as his release coated his hand.

“Ahhh,” Dean cried out, slapping his free hand against the wall. “Yes.” He matched Cas’ words as his own cum splashed against the shower wall.

Dean held tense as his cock pulsed, his breathing ragged as he came down from his high. Shame filled him as he dropped his forehead to the tile, trying to convince himself he didn’t just come to a fantasy of Cas.

It was a good thing he saved jerking off for last. Normally, he liked to start the shower with a few strokes, and keep himself turned on the whole time, teasing himself in between washing. Then, once he was finished, he would linger and let the water relax him in a way only a hot shower could. It was his favorite part of the day, and he had just ruined it.

Dean climbed out of the shower, refusing to admit he was probably more relaxed than he had been in quite some time. That was just an average shower on a totally normal day. And on normal days, with no hunts lined up, Dean liked to troll the bars. Despite having orgasmed less than ten minutes ago, he was planning his night out. He was going to find a blonde with green or dark eyes—anything but blue—and take her home and rock her world.

Dean slowly got dressed, imagining all the things he would do to her. Stripping her out of her bra, kissing her bare shoulders up to her neck. He imagined laying her down and kissing from her neck to her belly button. Dean was going to run his hand along her soft, wet folds, slipping in a finger as his kissed just below her stomach. He wanted to keep working his way down as his fingers slid in and out of her.

He pulled his boxers up his thighs as he planned out how he wanted to kiss the mystery woman’s thighs. Teasing her so his nose would gently brush against her most sensitive parts. He rubbed his hands along the insides of his thighs, pretending he was rubbing a woman just the same. After teasing her endlessly, he would finally start with slow gentle licks. He would catch her off guard, making her gasp. Dean loved the surprised sound of a woman getting her clit licked unexpectedly. Just a light roll of his tongue, and then he would pull back. Waiting until she reached down and grabbed his hair. That was always his sign that he had permission to go town. After teasing for so long, he would work his way quickly to bringing her to the edge. Listening to her pants and gaps. Feel her legs tense as she curled her toes, and just as she was about to explode, he would pull back blowing gently as he traced the outside of her clit with his thumb.

He could practically hear her whimpering, begging in a soft whisper to _please, just finish._ He would look up at her, devilish smile. Her artic blue eyes, staring back at him, soft cropped brunette hair stuck to a forehead full of sweat. He would look down again and wrap his lips around that big thick cock and—

_WHAT?_

Dean snapped back to reality, looking around his room, panting. What had he...? He was just daydreaming about eating out a blonde woman, so why the hell was Cas suddenly there with his monster cock? Dean had replaced the images of Cas’ smooth, pleasantly above-average cock with the giant dildo he had been using.

That was it. He wasn’t waiting for nightfall. With his best smile and a spritz of his most expensive cologne, he was capable of an early evening hookup. He took a moment to consider wearing his best fed suit and pretending to be some hot shot banker but decided against it. He wasn’t in the mood for buying ten dollar drinks all night. He wanted a frisky woman who would drink mid-shelf whiskey.

Dean got himself ready and packed an overnight bag. He was planning on driving into the closest city, getting an actual hotel room. Not some sleazy pay-per-hour dive room that they usually stayed in. He was going to get a room worth bribing someone back to.

Running away from his problems was something Dean did well, but it was especially hard to run when your problem was a six foot solid mass with two bright eyes, and hair that looked so soft you wanted to pillow your entire face in the downy strands. It was even more challenging when that large frame was blocking your doorway.

Dean had just yanked his door open, after hiking his overflowing bag high on his shoulder. Cas has been standing there, poised to knock on the door.

“Dean,” Cas gasped, his knuckles still lingering in the air. “You’re leaving?”

“Yeah, man. No case in over a week. I’m climbing the walls. Just thought I’d go out for the night.” Dean set his expression. Trying to keep all emotion from his face. He probably had an exact facial expression that said: “I’m running away because the real-life porn I saw you in is haunting me.” He was very expressive with his eyebrows.

“Oh, um okay.” Cas took his knuckles, that were still oddly hanging in the air, and lightly knocked them against Dean’s chin. “Knock ‘em dead, tiger,” the angel said, winking and scrunching up half his face in the process, before turning on his heel and marching across the hall to his room. Dean caught the tell end of Cas’ self-talk. “...tiger? What the…” was all he heard before the door slammed shut.

It made Dean smile, knowing he wasn’t the only one dealing with how uncomfortable they were around each other. A few days apart, and the whole mess will be far behind them.

  


Three hours and one hundred and fifty miles later had Dean’s shoulders relaxed. The tension he’d been carrying washed away sometime during the B side of _Dean’s Top 13 Zepp Traxx._ He made himself a copy when he was putting together the tape for Cas. Though the title was a bit of a lie. They were not his top thirteen tracks. They were the top songs Dean thought Cas would like or should know. The one time Dean got in Cas’ pimpmobile, he was blaring some Christian talk radio program. And while there wasn’t anything inherently wrong with that, Dean knew that Cas would be going out of his mind with all the inaccuracies and opinions preached as truth.

He smiled fondly, thinking about Cas’ annoyed scowl. His expressions were so minute, but they were there if you were looking. Not that Dean had been looking, he just happened to see them from time to time and had a good memory. Which was exactly why he couldn’t forget Cas succumbing to the pleasures of the flesh, right there in the bunker.

He decided the next town he passed would be the place to stop. There were a few towns on this stretch of highway. Nothing big, just your average small town in the desolate plains of Kansas. He wouldn’t have any problems finding a desperately lonely woman.

 

~~~~~

 

“That’s your third rejection tonight. You going for a record?” the bartender asked.

Dean glared at her, eyebrows drawn together and lips pursed tight.

“No need to get pissy. Maybe switch up your type. The blondes don’t seem to be working for you tonight, sugar,” the blue-eyed brunette said from her perch behind the bar.

“Maybe I have a type,” he grumbled, hunched over his fourth whiskey.

The bartender scoffed, “Yeah, I know your type.” She grabbed the bottle of Makers Dean had been working on and topped him off. He usually reserved the good stuff for nights when he wasn’t buying drinks for two, but after his first strikeout, he thought he might need to up his game.

“You know nothing about me.” Dean sipped his drink, blowing out a breath that felt like fire, trying to cool the burn in his throat.

“Sugar, I’ve been doing this a long time. I know enough. You’re a nomad, the reason don’t matter. You blow into town hoping a fresh face and a tight ass is all the work you’ll have to do.”

It had gotten late, later than Dean planned on, and the place was thinning out. The woman pulled out two shot glasses, poured and threw one back before pushing the second to Dean.

“What you don’t know is, these women ‘round here are used to your type. We are the only decent bar in three counties. They have their choice. And your pensive broody shoulders are chasing ‘em away.” She gave Dean a wink before walking further down the bar to help one of the remaining customers. Dean was pretty sure he wasn’t imagining the extra sway in her hips.

She was a beautiful woman. Light blue eyes, offset by her almost black hair. But that was exactly the type he was trying to avoid tonight. She had soft curves, supple breasts, and a little extra weight around the middle. Exactly what Dean wanted sitting on his lap, riding him like a mechanical bull.

He looked around the room, scoping out his options. It was a weeknight and all the respectable women were probably at home in bed. Good! Dean wasn’t looking for a respectable woman. He just wanted someone who didn’t resemble Cas. Not that the bartender looked like Cas. She had plump cheeks and her chin was too pointy. He could probably make it work. It’s not like he was going to be thinking about what he saw Cas doing while he was with her.

Dean sat up straighter, trying to get her attention. He didn’t want to do a complete shift on her, so he kept his shoulders slightly broody.

“Hey sweetheart, can I get another?” Dean asked polishing off the rest of the whiskey.

She eyed him suspiciously, “Sure thing.” She poured him a glass and put the bottle back on the shelf.

Dean tracked her movements. She hadn’t put the bottle up since he ordered his first drink. This couldn’t be a good sign, she was probably going to kick him out.

He resigned himself to having to try a different bar, maybe even a different town. There was no sense in lingering. He only had a few hours before last call, so he needed to hit the road.

Before he could ask for his bill, she was dropping his check and credit card down in front of him. He was dreading what several hours of Makers Mark and Cosmopolitans would cost him. He was surprised to see he’d been charged for old Rock Gut all night, and apparently, he had been talking up women who drank shots of vodka. What was more surprising was a phone number scribbled across the top of his customary copy.

_Told ya...I’m a sure thing. 502-589-4313_

Dean looked at her, eyes bulging. Not two minutes ago she was making fun of him for being desperate, now she was offering herself over.

“Don’t look so shocked, sugar. I’m not passin’ up a hot piece like you, just because you’re kickin’ me out when it’s over.” She leaned across the counter, cleavage on full display. “Now, go back to your room, take a shower, and text me the hotel and room number and I’ll be there when I’m off. Oh, and make sure you get nice and clean. I feel like eating out tonight.”

Dean started to sputter, choking on air. The bartender—fuck, he didn’t even know her name—threw her head back and laughed. “Oh, this is going to be fun,” she said. Walking off without giving him a second glance.

~~~~~

 

“I swear this has never happened to me before.” Dean pulled the blanket up higher around his waist.

“It’s okay, it happens to everyone,” the still nameless bartender said.

Dean groaned. “No it doesn’t, not to me. I fucking jerked off this morning.”

He slapped his palm against his face. That didn’t make his case any stronger.

“Look, some guys don’t like it. I figured you would—”

“It’s not that. I really fucking liked that. I think that’s my problem.” He gripped the scratchy comforter, trying not to think about all the people who fucked on it before him. Or at least, his _attempt_ to fuck on it.

“It’s okay, dude. I’m not going to think you’re a homophobe or anything ‘cause you went limp while I ate you out.” She sounded so sympathetic, it made him ten times more embarrassed.

“Hey, I was hard until uh…” Dean trailed off. As he replayed the moment over he realized that when he was on his elbows, ass in the air, he was hard as a rock. The warm tongue swiping, sucking, and prodding had him on the edge. For all the kinky shit he’d done in his past, he never had anyone willing to eat him out. It wasn’t usually a stranger’s go-to move. But fuck if he didn’t love it.

The problem wasn’t her tongue or the finger that slipped in as she circled his hole. It was when he turned back to look at her she was...well, a her.

He had been moaning and writhing against the bed, so lost in pleasure that he forgot who he was with. He only realized, laying next to this beautiful woman, that he had been expecting—wanting— to see Cas.

“Stop looking like I kicked your puppy, and just tell me about ‘em.” She walked across the room. Sliding into her panties and hooking her bra from behind. It always impressed him that women could line up those stupid little clasps without even looking.

“There’s not a ‘them’,” he squeaked and dropped his head back against the headboard. Now, not only was his dick acting like a prepubescent teen, his voice was too.

“Okay. I can go, and you can sit here and wallow in self-pity, wishing I was someone else. Or you can crack open that pint of Jack I see sitting on your dresser and you can tell me, a perfect stranger that you’ll never see again, all about her. Or him. I don’t judge.”

The woman stood there in the middle of the dingy hotel room looking beautiful. She was tough, but still sweet. Someone Dean could picture himself within those rare moments he let himself pretend a hookup could be more than one night. And she had a good point. He could work out the shit going on with Cas and then go home and everything would be back to normal.

“Yeah, Okay.” Was all he got out before she snagged up his boxer and his black undershirt. She threw his boxer at him and dropped his shirt over her body.

“What?” she asked at Dean’s confused gaze. “I’m not getting laid and you smell good. At least let me have this part.” She turned, remembering the whiskey before plopping down next to Dean. “I’d say I at least deserve the post-sex cuddling, but you don’t really seem like the type.”

He was kind of disheartened to learn he was so transparent. “You know, usually women find me mysterious and sexy.” He reached around her waist pulling her closer. If he was going to admit to his most embarrassing moment, it would be easier to talk into her hair than her face.

“You got the sexy thing right, but you’re not mysterious. Women just let you believe they think that. It’s easier. Stop stalling and tell me.” She laid her head against his chest and sighed. Dean imagined her being as lonely as he was. If she was willing to take a chance on him after watching him strikeout all night, she might have needed the company as much as he had. Though he doubted she saw her best friend riding a fake cock stuck to their headboard, and then couldn’t get the image out of her mind.

“So, I have this friend. Well, he’s my best friend—”

“Ha, I knew it was a guy.”

“Anyway,” Dean rolled his eyes, “I, uh, walked in on him while he was, um, you know busy.”

The bartender took a long pull from the whiskey and passed the bottle to Dean. His head was still light from the earlier drinks, but he took a swig, thinking about loose lips.

“You didn’t knock?”

“Yes, I knocked. But he said “yes”. It’s the universal word for come in.” He took one more sip before passing the bottle back to her.

“No, it’s not.”

“Yes, it is. Everyone knows ‘yes’ means coming in.”

“Agree to disagree. Go on.” She rolled her wrist telling him to hurry up.

“So, I walk in and he’s got a huge fucking dildo stuck to his headboard, right? And he’s just going at it. He’s moaning, and stroking his dick so hard it’s about to catch fire. And just as he looks up at me, his stupid perfect blue eyes staring at me. And I’m just standing there in shock, and then bam, he comes all over himself. I mean it’s dripping down his hand onto the bed. And this fucker just asks ‘is there something you needed’. Yeah, there was something I needed. I needed to never see my angel best friend rubbing one out with a plastic dick in his ass.” Dean’s breath was coming in shallow pants.

“Angel?”

Dean shifts, eyes dropping down to the bed. “Oh yeah, uh, he um, he’s—”

“Oh my god, you don’t actually get it, do you?” she asked getting to her knees and crawling closer to Dean.

“Get what?”

“Let me guess, you jacked off in, probably the shower, so typical, and tried your damnedest to not think of him, but as soon as come started shooting, his face was all you saw.” She looked at Dean, one perfectly sculpted brow raised.

Dean rubbed the back of his neck. “It didn’t happen exactly like that.”

She flopped over, laying down next to him again. “Oh honey, you’ve got it bad and didn’t even know.”

“What? No, I don’t.” Dean’s brows furrowed and his eyes shot back and forth. “No. I mean I don’t. I can’t. He’s, well he’s. I’m not…”

“Apparently, he is, and you are.” She smiled up sweetly at him. There was no malice behind her words, she was simply telling Dean that he had a crush on his best friend. Which he didn’t, because he’s not a fifteen-year-old girl.

“Nah. I just happened to remember him. That’s all.”

“Just one more guess, if I may. He’s got blue eyes and dark hair? It’s why you wouldn’t look at the cute brunette who was begging for your attention when you first got there. It’s why you were only after petite blondes?”

Dean sat up, the comforter falling down to his waist. “Petite wasn’t on the list,” he mumbled.

“So what, you’ve got a hard-on for your best friend. Who, by the way, happens to like taking it. Ask him out.”

“What?” Dean almost gave himself whiplashed he turned so quickly. “I can’t just ask him out. I’m not even gay. Or Bisexual, or whatever. And neither is he.”

“I don’t know, if the dildo was as big as you say it was, he’s probably a little less straight than you expected. And so are you.”

She got up and pulled off his shirt. Dropping it next to him. It smelled like their combined scents, and he wished the room smelled of them and sex. He wished she never touched his ass, and they would have just had sex the boring old-fashioned way. At least then he wouldn’t be questioning both his and Cas’ sexuality.

“Look, don’t freak out. If you like the guy, you like him. If you don’t, you don’t. But don’t let a stupid label keep you from being with someone you care about. Talk to him. Feel it out, and see where it goes. Otherwise, you’ll probably be letting girls down all across the country.”

She leaned down and kissed his forehead. He wanted to get up and walk her out. Pay for her a cab, or at least make sure she was sober enough to drive herself home. Instead, all he did was sit in between an itchy comforter and stiff sheets wondering what he felt for Cas.

It wasn’t like he thought anything was wrong with being gay or bisexual or whatever. But it just wasn’t how he labeled himself. He loved fucking women. He loved big breasts, wide hips, and thick thighs. Or small breasts and thin hips. It didn’t matter that much to him.

It wasn’t the idea of being with a man that had him so hung up. Which was surprising. But he watched enough porn that it was at least understandable that he could mentally replace himself with one of the actors.

But when he tried to replace both actors with himself and Cas his insides squirmed. He didn’t feel disgusted, and it’s true part of the feeling was excitement, but more than anything he felt like he was violating Cas.

The bartender was wrong just because Cas liked using a dildo didn’t mean he would want to be with a man. And even if he liked men, there was no way he would want to be with Dean. Would he?

They had always been closer than Cas and Sam. They talked about everything, and Cas had a way of always soothing him when he was most upset. Not to mention all the staring and lack of personal space. But none of that added up to sexual interest. But, fuck, if Cas could do what the bartender was doing, he would be in heaven.

Dean choked on a laugh. He just equated an angel eating his ass to heaven. But he’s been to heaven, and the comparison wasn’t wrong.

Though Dean often drove while drinking, he knew his limits, and he was far too gone to get behind the wheel. So instead, he reached over and polished off what was left of the Jack before switching off the dim yellow light, and snuggling deeper into the mattress. He was on the pleasant side of drunk where his limbs felt heavy and his mind foggy, but his stomach didn’t beg for relief.

He closed his eyes and for the first time since he’d seen Cas naked, let himself remember every detail he could conjure. The way Castiel’s hair was plastered to his forehead, sweat glistening at his temples. The breathy way he said ‘yes’ before Dean opened the door. His long elegant fingers wrapped around his pulsing cock.

Without permission, a small whimper escaped his throat as he recalled Cas coating his hand in cum. He had been fucking himself hard against the dildo, knocking the headboard against the wall. It was better than any masturbation porn he had ever seen, and he couldn’t help brushing his fingers over his swelling cock.

The air in the room was cool, causing his goosebumps to ripple across his skin. He mentally replaced the sex toy with himself behind Cas, gripping his hips as the angel thrust back into him. It was enough to make Dean grip himself and give a strong tug. This time he didn’t try and stop the images. He let visions of licking, sucking, nipping, and squeezing fill his mind and he stroked himself with fervor.

Before long Dean was moaning as spurts of cum splashed across his heaving chest. He screwed his eyes shut and rode as the ecstasy holding himself, wishing it was Cas’ hand on him.

He didn’t make any real attempt at cleaning up, just wiping himself off with the opposite corner of the sheet before falling against the pillows. It had been a long confusing day, and he was drifting off to sleep to plans of working things out with Cas.

 

~~~~~

 

Dean walked into the bunker with the same determination he used when on a hunt. Scared, but resigned by duty. He had to talk to Cas about what he saw. He wanted to feel things out and get a sense for what Cas was thinking. He considered offering a ‘friends with benefits’ situation, but he knew that wouldn’t work. They were both jealous and possessive people, and even now the thought of Cas with someone else made him testy.

If he knew Cas as well as he thought he did, he guessed Cas would ask questions about what Dean did for pleasure. What Dean wasn’t sure of, was if Cas was going to play the innocent version of himself where he pretended to not understand humans in order to get Dean to do something for him. Or if he was going to play aloof and pretend it was totally normal to talk masturbation with your best friend. The third option and the one Dean hoped for, was Cas getting flustered, and pretending it was no big deal. He was a terrible liar, and Dean could usually see right through his facade. Dean hoped his avoidance meant Cas felt just as much about it as he did.

He had called Sam on his way home, but his brother was a few hours away, off watching some french movie that had subtitles. As casually as possible, he asked if Cas was home, but Sam was no help. He hadn’t seen the angel all day and wasn’t paying attention to the cars when he left. The upside was Sam wasn’t home to somehow overhear them talk. The downside was that Sam wasn’t home, and he might be stuck in Awkwardville for the next twenty-something hours.

“Cas?” Dean shouted as the heavy metal door clinked shut behind him. His dirty boots echoed as he made his way down the iron stairs. “Hey, buddy. You here?”

There was no answer as Dean scoped out the library. Books were scattered across the table. It’s wasn’t like Sam to leave his research out, so Dean assumed Cas was the one working in there.

A loud grunt reverberated through the empty halls. The hair on Dean’s neck stood up and he quietly pulled his gun from the back of his waistband. With silent footfalls, he crept down to the living quarters. Cas grunted again. There was no mistaking it this time, something had him. He sounded so pained and distressed.

He wanted to run to Cas but knew a surprised attack on whatever had a hold of him would have the best outcome. One quick bullet and they would be stunned, then he’d pull his angel blade and drop whatever was in Cas’ room.

He was working out the last detail of his plan, wishing he had a thigh holster for his blade, when he peeked around the corner. Cas’ door was open, and Dean could hear him panting. Whatever had him sounded dangerous.

Both hands were on his gun as he took a deep breath, stepping out in front of Cas’ open door. Instead of an unimaginable monster pinning his friend down, sucking the life out of him. Dean saw a very naked Cas on his back with his legs high up in the air, ankles crossed. He was pushing that same plastic, foot long cock into himself, panting and groaning as he stretched forward to reach.

Dean dropped his hands and let them dangle at his side. Cas didn’t notice him and all Dean could do was stare. He imagined talking about what he saw. Maybe even opening up about Cas and his preferences. And if all went well they could discuss trying things out on each other. What Dean didn’t plan for was Cas folded in half, fucking himself so hard his grunts sounded as though he was being tortured. And oh God, that was a whole other side of sex Dean hadn’t meant to bring up, but couldn’t help wondering if Cas liked it rough.

There was nothing he could do. His limbs were weighed and instead of telling him to abort, his traitorous mind was encouraging him to go help. Cas was in a perfect pose to walk up to him, pull the dildo out of his ass and throw it in the trash. He could drop to his knees at the foot of the bed and swipe his flat tongue across Cas’ stretched hole.

His dick was throbbing in his jeans just thinking about holding Cas’ crossed ankles up with one hand, while his tongue danced and played across Cas’ most intimate entrance.

He couldn’t contain his whine as he pawed at his cock. Everything up until now had been hypothetical. A situation he was mostly sure he would avoid once he got home. But as Cas pulled the dildo out—sitting up on his elbows, bending his knees until his heels touched his ass—he knew there was no stopping it. They could talk later, right then Dean needed to taste Cas. Feel the heat from his body as skin met skin.

There must have been something in Dean’s face or body language because Cas met him with a mischievous gaze, lifting one brow, challenging him before letting himself fall back against the bed. He straightened his legs up in the air before crossing his ankles once more. Cas peeked around his legs and grinned at Dean before swiping a glistening finger across his hole.

Dean gasped as Cas’ finger disappeared and grabbed the hem of his shirt ripping it off over his head. There was nothing more he wanted than to grab Cas by the hips and pull his ass into his face. And that’s exactly what he did.

Without a word, he was on his knees tongue ghosting over Cas. There was a part of him that was worried it would be less than clean or taste weird but to his delighted surprise, Cas just tasted like skin...warm, sensual, beautiful skin.

His hands gripped Cas’ ass, blunt nails digging in and leaving crescent moon shaped marks. He pulled, tugged, and smacked Cas’ cheeks as his mouth worked his way from the angel’s ass to his balls.

Dean took ahold of Cas’ meaty thick thighs and kissed each one gently before roughly pulling them apart. Cas moaned and bucked up, letting his legs fall to the side. He looked so debauched staring up at Dean, his hard fat cock resting against his stomach. He couldn’t decide what he wanted. Cas was laid out for him like a dessert buffet and he was ready to taste every treat the man had to offer. But he was achingly hard and because of Cas’ earlier prep, he was ready to take him.

He took a moment for himself to look Cas over. He was scared once he did this there was not going back. Though, he was pretty sure he just hit the top ten gayest thing a straight guy could do and got insanely turned on by it. He was already past the point of no return.

“Can I?” Dean asked his hands on the button of his jeans. He thrust forward to make sure Cas wasn’t missing any clues, rubbing the denim against Cas’ thighs.

“Yes. Please. Please, fuck me, Dean,” Cas cried, reaching down to rub his red glistening cock.

“Fuck,” Dean growled pulling his pants and boxers down in one swift move. Cas had healed him of concussions, broken bones, and even flipped out once and healed a paper cut. So Dean was sure if he picked up an STI since his last checkup—which was unlikely since he hadn’t actually been with anyone—he was sure Cas could heal them both of that too.

He took the other man’s legs and rested them on his shoulders, kissing a trail from his toes to his knee. “You sure?” He looked down as his best friend. Cas was smiling and his eyes were bright.

“Only if you are.”

Dean placed another gentle kiss on Cas’ calf before gripping himself and slowly pushing into Cas’ tight heat.

“Fuck,” Dean hissed as he felt Cas’ silky smooth passage. “This isn’t going to last long. If you give me a do-over, I promise it will be better.”

Cas’ mouth twitched and he nodded enthusiastically. He couldn’t imagine what his friend was thinking in the moment, but he wanted to fuck the thoughts right out of his head.

He pulled back and pushed in slowly a few times reveling in the feel of Cas, before he picked up the pace. He already felt his orgasm building and needed Cas to come as quickly as he did so he didn’t feel embarrassed.

He guided one of the other man’s legs down to the bed and took Cas’ cock in his hand. Giving a firm squeeze before stroking hard and fast, his hips matching the rhythm. Castiel let out a gravely moan as he brought his hands up by his head gripping the sheet.

Dean fucked into him, hips gyrating back and forth while he stroked Cas’ swollen cock in tandem. “Oh fuck, Cas, please tell me you’re close,” Dean begged.

“If you just shift your hips,” Cas wiggled a little before crying out, “Yes. There. Oh, Dean harder.”

Dean grinned knowing what he found and pushed into Cas as hard as he could, not thrusting in and out, but rocking his hips up and forward, rubbing as much of his cock as he could over Cas’ prostate, all while never letting his hand slow.

“Dean, please. Don’t know. I’m so…” Cas trailed off, rubbing his hand over Dean’s, stroking along with him.

Cas’ eyes screwed up tight and his back arched off the bed as he growled out Dean’s name, cum shooting between them. Dean looked down, his hand covered in his best friend’s come. Getting Cas off turned him on and he was coming in just a few more rolls of his hips. He felt the tingling work it’s way slowly through his body, the muscles in his abdomen clenching. He whispered Cas’ name as he filled his best friend full of his release.

Dean slumped forward, his feet sliding back against the floor. He was panting and covered in sweat. The afterglow didn’t last long, as Cas start to shift around. He had never felt anything better, and it seemed like Cas wanted it, but part of him was worried Cas was just appeasing him.

“Um, Dean?” Cas said, stroking his hand through Dean’s hair.

“H’mm?”

“I, ah, can’t feel my leg,” Cas said with a slight hesitation in his voice.

Dean jerked back, inadvertently pulling out, causing Cas to gasp. Dean couldn’t pull his eyes away from the cum trickling out of Cas’ ass.

“Hey, come here.” Cas’ eyes were soft, and he still had the hint of a smile. “Please.”

On the way home, Dean imagined talking to Cas, for it to be easy like some of his normal confessions were. _I’m scared, I’m lonely, I miss you, I miss my mom_. Those all rolled off his tongue when he was ready to talk. He thought the sex would be the hard part. He imagined being awkward and uncomfortable. Questioning himself and his sexuality. In hindsight, it didn’t make sense. He was good at sex and struggled with talking, and wasn’t sure why he imagined it to be the reverse with Cas.

He had an instinct to clean Cas up. To care for him after using him so harshly, so he reached for his t-shirt and did the best he could to clear Cas of the evidence of what they had just done. At Cas’ request, he sat down next to him. Cas shifted up the bed, and pull a hand on Dean’s shoulder, pulling him back so he was resting against Cas. Dean felt his body relax as Cas’ hand ran up and down his arm. He was soothed by the touch, and let Cas’ body take his full weight.

“Dean, come here. Get comfortable,” Cas said. His voice was deep and commanding, and Dean wanted to obey. He didn’t say anything as he shifted his body and laid on his side next to Cas. The angel snaked his arm around Dean’s neck and shoulder and pulled him down on his chest.

“We don’t have to talk about it.” He felts Cas’ deep rumble against his ear. It was probably the best thing he’d ever heard, and it gave him the courage to move forward.

“I want to, you know, talk about it at some point. But for now, can we just agree we will be doing this again?” Dean’s voice was soft, lacking his usual bravado.

Cas huffed a laugh. “Dean, we can do this anytime you want. We can do anything you want. I’ll take you in any way I can have you.” Cas leaned down and kissed the top of his head.

“Good, because you can have me any way you want.” Dean scooted closer to Cas, wrapping his arms around Cas’ ribs and holding him as if his life depended on it.

Dean lay there for a few moments before he felt a hand tipping his face up. “Can I kiss you,” Cas asked. Dean nodded and stretched his neck, gently brushing over Cas’ lips. It wasn’t an earthshattering kiss, he imagined that would come later, as they explored each other’s wants and needs. This was a sweet kiss. One that said everything was okay, they were okay, and both enjoyed what they just did.

He laid back down on Cas’ chest, the other man drawing patterns on his back with his fingertips. For all the times he had been scared, hurt, and alone, Dean finally felt safe.

 


End file.
